Long-Term Stability Study of L-Adrenaline Injections: Kinetics of Sulfonation and Racemization Pathways of Drug Degradation

Journal of Pharmaceutical Sciences

Volumn 93, Issue 4, 2004, Pages 969-980

  Stepensky, David ^a   Chorny, Michael ^a   Dabour, Ziad ^a   Schumacher, Ilana ^a  

^a Medical Corps Mil   (Israel)

Author keywords

Adrenaline; Chirality; HPLC (high performance liquid chromatography; Stability

Indexed keywords

ADRENALIN; ADRENALIN SULFONATE; ALUMINUM; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

AMPOULE; ARTICLE; CHIRALITY; DEGRADATION KINETICS; DRUG FORMULATION; DRUG INACTIVATION; DRUG STABILITY; DRUG STORAGE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PH; PROSPECTIVE STUDY; RACEMIZATION; REGRESSION ANALYSIS; SULFONATION; VALIDATION PROCESS;

EID: 1842482444     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1002/jps.20010     Document Type: Article

References (20)

1. Harper HA. 1975. Review of physiological chemistry, 15th ed. Los Altos California: Lange Medical Publications. p 471.
2. Backe-Hansen K, Aarnes ED, Vennerod AM, Jensen KB. 1963. On the stability of adrenaline in injections: A comparison of chemical and bioassay methods. J Pharm Pharmacol 15:804-809.
3. Backe-Hansen K, Holst G, Vennerod AM, Briseid K. 1966. Stability of adrenaline in injections. Report of a 5-year storage test. Acta Pharm Suec 3:269-272.
4. Lundgren P, Strom S. 1966. Stability of adrenaline in 0.1% solutions. Experience from production control. Acta Pharm Suec 3:273-280.
5. Taylor JB, Scharma SC, Simpkins DE. 1984. Effect of sodium metabisulfite and anaerobic processing conditions on the oxidative degradation of adrenaline injection BP. Pharm J 242/243:646-648.
6. Connors KA, Amidon GL, Stella VJ. 1986. Chemical stability of pharmaceuticals. A handbook for pharmacists. 2nd ed. Epinephrine: John Wiley & Sons. pp 438-447.
7. Thoma K, Struve M. 1986. Untershung der stabilitat handelsublicher adrenalin-losungen. Pharm Acta Helv 61(3):66-68.
8. Fyllingen G, Langvik TA, Hasselgard P, Roksvaag PO. 1990. Racemization and oxidation in adrenaline injections. Acta Pharm Nord 2(5):355-362.
9. Grubstein B, Milano E. 1992. Stabilization of epinephrine in a local anesthetic injectable solution using reduced levels of sodium metabisulfite and EDTA. Drug Devel Indust Pharm 18(4):1549-1566.
10. Higuchi T, Schroeter L. 1960. Kinetics and mechanism of formation of sulfonate from epinephrine and bisulfite. J Am Chem Soc 82:1904-1907.
11. The United States Pharmacopeia, 26th ed. 2003. Rockville, MD: Pharmacopeial Convention, Inc. p 709.
12. Kirchhoefer RD, Sullivan GM, Allgire JF. 1985. Analysis of USP epinephrine injections for potency, impurities, degradation products, and d-enantiomer by liquid chromatography, using ultraviolet and electrochemical detectors. J Assoc Off Anal Chem 68(2):163-165.
13. Shpigun OA, Shapovalova EN, Ananieva IA, Pirogov AV. 2002. Separation and enantioseparation of derivatized amino acids and biogenic amines by high-performance liquid chromatography with reversed and chiral stationary phases. J Chromatogr A 979:191-199.
14. Analytical techniques for graphite furnace atomic absorption spectrometry. Ueberlingen, Germany: Bodenseewerk Perkin Elmer GmbH. 1984.
15. Zar JH. 1984. Confidence intervals in regression: Biostatistical analysis, 2nd ed. Englewood Cliffs, New Jersey: Prentice-Hall. pp 272-276.
16. D'Argenio DZ, Shumitzky A. 1997. ADAPT II user's guide: Pharmacokinetic/pharmacodynamic systems analysis software. Los Angeles: Biomedical Simulations Resource.
17. Gabrielsson J, Weiner D. 1997. Pharmacokinetic and pharmacodynamic data analysis: Concepts and applications, 2nd ed. Stockholm: Swedish Pharmaceutical Press.
18. Milano EA, Waraszkiewicz SM, Dirubio R. 1982. Aluminum catalysis of epinephrine degradation in lidocaine hydrochloride with epinephrine solutions. J Parenteral Sci Technol 36(6):232-236.
19. Allgire JF, Juenge EC, Damo CP, Sullivan GM, Kirchhoefer RD. 1985. High-performance liquid chromatographic determination of d-/l-epinephrine enantiomer ratio in lidocaine-epinephrine local anesthetics. J Chromatogr 325(1):249-254.
20. Venter DP. 1991. The acid-catalyzed racemization mechanism of catecholamines. Tetrahedron 47(27): 5019-5024.